2-alkyl-cycloalk(en)yl-carboxamides

ABSTRACT

Novel 2-alkylcycloalk(en)ylcarboxamides of the formula (I) 
     
       
         
         
             
             
         
       
         
         in which 
         X, s, R 1 , L, R 2  and A are as defined in the description, 
         a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

The present invention relates to novel 2-alkylcycloalk(en)ylcarboxamides, to a plurality of processes for their preparation and to their use for controlling unwanted microorganisms.

It is already known that numerous carboxamides have fungicidal properties (cf., for example, WO 98/03495, WO 98/03486 and EP-A 0 589 313). Thus, some 2-alkylcycloalkylcarboxamides are already known, such as, for example, N-(2-sec-butylcyclohexyl)-2-methyl-4,5-dihydrofuran-3-carboxamide from WO 98/03495, N-[2(2-ethylbutyl)cyclohexyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide from WO 98/03486 and N-2-sec-butylcyclohexyl)-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide from EP-A 0 589 313. The activity of these compounds is good; however, in some cases, for example at low application rates, it is unsatisfactory.

This invention now provides novel 2-alkylcycloalk(en)ylcarboxamides of the formula (I)

in which

-   X represents —CR³R⁴R⁵ or —SiR⁴⁹R⁵⁰R⁵¹, -   s represents 1 or 2, -   R¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,     C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;     C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,     C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine     and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,     (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,     (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;     halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,     halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13     fluorine, chlorine and/or bromine atoms; -    (C₁-C₈-alkyl)carbonyl, (C₁-C₈-alkoxy)carbonyl,     (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, (C₃-C₈-cycloalkyl)carbonyl;     (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl,     (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,     (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,     chlorine and/or bromine atoms; or —C(═O)C(═O)R⁶, —CONR⁷R⁸ or     —CH₂NR⁹R¹⁰, -   L represents L¹ or L², -   L¹ represents C₃-C₇-cycloalkyl-1,2-ene (C₃-C₇-cycloalkyl-1,2-diyl)     which is optionally mono- to tetrasubstituted by identical or     different substituents from the group consisting of fluorine,     chlorine, C₁-C₄-alkyl and C₁-C₄-haloalkyl, -   L² represents cyclohexenylene (cyclohexenediyl) which is optionally     mono- to tetrasubstituted by identical or different substituents     from the group consisting of fluorine, chlorine, C₁-C₄-alkyl and     C₁-C₄-haloalkyl, -   R² represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl     having 1 to 9 fluorine, chlorine and/or bromine atoms, -   R³ represents halogen, C₁-C₈-alkyl or C₁-C₆-haloalkyl having 1 to 13     fluorine, chlorine and/or bromine atoms, -   R⁴ represents halogen, C₁-C₈-alkyl or C₁-C₆-haloalkyl having 1 to 13     fluorine, chlorine and/or bromine atoms, -   R⁵ represents hydrogen, halogen, C₁-C₈-alkyl or C₁-C₆-haloalkyl     having 1 to 13 fluorine, chlorine and/or bromine atoms, -   R³ and R⁴ furthermore together with the carbon atom to which they     are attached form a 3- to 6-membered carbocyclic or heterocyclic,     saturated or unsaturated ring which is optionally substituted by     halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or     C₁-C₄-haloalkoxy, -   R⁴⁹ and R⁵⁰ independently of one another represent hydrogen,     C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄-alkylthio-C₁-C₄-alkyl or C₁-C₄-haloalkyl, -   R⁵¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,     C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,     C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,     C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, or represents in each case     optionally substituted phenyl or phenylalkyl, -   R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,     C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl,     C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine     and/or bromine atoms, -   R⁷ and R⁸ independently of one another each represent hydrogen,     C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;     C₁-C₈-haloalkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl     having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, -   R⁷ and R⁸ furthermore together with the nitrogen atom to which they     are attached form a saturated heterocycle having 5 to 8 ring atoms     which is optionally mono- or polysubstituted by identical or     different substituents from the group consisting of halogen and     C₁-C₄-alkyl, where the heterocycle may contain 1 or 2 further     non-adjacent heteroatoms from the group consisting of oxygen,     sulphur and NR¹¹, -   R⁹ and R¹⁰ independently of one another represent hydrogen,     C₁-C₈-alkyl, C₃-C₈-cycloalkyl; C₁-C₈-haloalkyl, C₃-C₈-halocycloalkyl     having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, -   R⁹ and R¹⁰ furthermore together with the nitrogen atom to which they     are attached form a saturated heterocycle having 5 to 8 ring atoms     which is optionally mono- or polysubstituted by identical or     different substituents from the group consisting of halogen and     C₁-C₄-alkyl, where the heterocycle may contain 1 or 2 further     non-adjacent heteroatoms from the group consisting of oxygen,     sulphur and NR¹¹, -   R¹¹ represents hydrogen or C₁-C₆-alkyl, -   A represents the radical of the formula (A1)

-    in which     -   R¹² represents hydrogen, cyano, halogen, nitro, C₁-C₄-alkyl,         C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₃-C₆-cycloalkyl,         C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio having         in each case 1 to 5 halogen atoms, aminocarbonyl or         aminocarbonyl-C₁-C₄-alkyl,     -   R¹³ represents hydrogen, halogen, cyano, C₁-C₄-alkyl,         C₁-C₄-alkoxy or C₁-C₄-alkylthio,     -   R¹⁴ represents hydrogen, C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl,         C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl         having in each case 1 to 5 halogen atoms, or phenyl, -   or -   A represents the radical of the formula (A2)

-    in which     -   R¹⁵ and R¹⁶ independently of one another represent hydrogen,         halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen         atoms,     -   R¹⁷ represents halogen, cyano or C₁-C₄-alkyl, or C₁-C₄-haloalkyl         or C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A3)

-    in which     -   R¹⁸ and R¹⁹ independently of one another represent hydrogen,         halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen         atoms,     -   R²⁰ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A4)

-    in which

R²¹ represents hydrogen, halogen, hydroxyl, cyano, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio having in each case 1 to 5 halogen atoms,

-   or -   A represents the radical of the formula (A5)

-    in which     -   R²² represents halogen, hydroxyl, cyano, C₁-C₄-alkyl,         C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl,         C₁-C₄-haloalkylthio or C₁-C₄-haloalkoxy having in each case 1 to         5 halogen atoms,     -   R²³ represents hydrogen, halogen, cyano, C₁-C₄-alkyl,         C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy         having in each case 1 to 5 halogen atoms, C₁-C₄-alkylsulphinyl         or C₁-C₄-alkylsulphonyl, -   or -   A represents the radical of the formula (A6)

-    in which     -   R²⁴ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5         halogen atoms,     -   R²⁵ represents C₁-C₄-alkyl,     -   Q¹ represents S (sulphur), O (oxygen), SO, SO₂ or CH₂,     -   p represents 0, 1 or 2, where R²⁵ represents identical or         different radicals if p represents 2, -   or -   A represents the radical of the formula (A7)

-    in which     -   R²⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5         halogen atoms, -   or -   A represents the radical of the formula (A8)

-    in which     -   R²⁷ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5         halogen atoms, -   or -   A represents the radical of the formula (A9)

-    in which     -   R²⁸ and R²⁹ independently of one another represent hydrogen,         halogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5         halogen atoms,     -   R²⁰ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A10)

-    in which -   R³¹ and R³² independently of one another represent hydrogen,     halogen, amino, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5     halogen atoms, -   R³³ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl     having 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A11)

-    in which     -   R³⁴ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,         di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms,     -   R³⁵ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1         to 5 halogen atoms, -   or -   A represents the radical of the formula (A12)

-    in which     -   R³⁶ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,         di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms,     -   R³⁷ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1         to 5 halogen atoms, -   or -   A represents the radical of the formula (A13)

-    in which     -   R³⁸ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1         to 5 halogen atoms, -   or -   A represents the radical of the formula (A14)

-    in which     -   R³⁹ represents hydrogen or C₁-C₄-alkyl     -   R⁴⁰ represents halogen or C₁-C₄-alkyl, -   or -   A represents the radical of the formula (A15)

-    in which     -   R⁴¹ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5         halogen atoms, -   or -   A represents the radical of the formula (A16)

-    in which     -   R⁴² represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A17)

-    in which     -   R⁴³ represents halogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,         C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio or         C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A18)

-    in which     -   R⁴⁴ represents hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl         having 1 to 5 halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl,         hydroxy-C₁-C₄-alkyl, C₁-C₄-alkylsulphonyl,         di(C₁-C₄-alkyl)aminosulphonyl, C₁-C₆-alkylcarbonyl or in each         case optionally substituted phenylsulphonyl or benzoyl,     -   R⁴⁵ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms,     -   R⁴⁶ represents hydrogen, halogen, cyano, C₁-C₄-alkyl or         C₁-C₄-haloalkyl having 1 to 5 halogen atoms,     -   R⁴⁷ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl         having 1 to 5 halogen atoms, -   or -   A represents the radical of the formula (A19)

-    in which -   R⁴⁸ represents C₁-C₄-alkyl.

Furthermore, it has been found that 2-alkylcycloalk(en)ylcarboxamides of the formula (I) are obtained when

-   (a) carboxylic acid derivatives of the formula (II)

-    in which     -   A is as defined above and     -   X¹ represents halogen or hydroxyl,     -   are reacted with aniline derivatives of the formula (III)

-   -   in which X, s, R¹, L and R² are as defined above, if appropriate         in the presence of the catalyst, if appropriate in the presence         of a condensing agent, if appropriate in the presence of an acid         binder and if appropriate in the presence of a diluent, or

-   (b) 2-alkylcycloalk(en)ylcarboxamides of the formula (I-a)

-    in which X, s, L, R² and A are as defined above, -    are reacted with halides of the formula (IV)     R^(1A)—X²  (IV) -    in which     -   R^(1A) represents C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,         C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,         C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,         halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl having in         each case 1 to 9 fluorine, chlorine and/or bromine atoms;         formyl, formyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,         (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;         halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,         halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to         13 fluorine, chlorine and/or bromine atoms;         (C₁-C₈-alkyl)carbonyl, (C₁-C₈-alkoxy)carbonyl,         (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, (C₃-C₈-cycloalkyl)carbonyl;         (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl,         (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,         (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9         fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R⁶,         —CONR⁷R⁸ or —CH₂NR⁹R¹⁰,     -    R⁶, R⁷, R⁸, R⁹ and R¹⁰ are as defined above,     -   X² represents chlorine, bromine or iodine,     -   in the presence of a base and in the presence of a diluent.

Finally, it has been found that the novel 2-alkylcycloalk(en)ylcarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials.

If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also in the form of tautomers. What is claimed are both the E and the Z isomers, and the threo and erythro and also the optical isomers, any mixtures of these isomers and the possible tautomeric forms.

The formula (I) provides a general definition of the 2-alkylcycloalk(en)ylcarboxamides according to the invention. Preferred radical definitions of the formulae mentioned above and below are indicated below. These definitions apply to the end products of the formula (I) and likewise to all intermediates.

-   X preferably represents —CR³R⁴R⁵. -   X furthermore preferably represents —SiR⁴⁹R⁵⁰R⁵¹. -   s preferably represents 1. -   s furthermore preferably represents 2. -   s particularly preferably represents 1. -   R¹ preferably represents hydrogen, C₁-C₆-alkyl,     C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,     C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,     C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,     C₁-C₄-haloalkylsulphonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,     C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine     and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,     (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,     (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;     halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,     halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13     fluorine, chlorine and/or bromine atoms; -    (C₁-C₆-alkyl)carbonyl, (C₁-C₄-alkoxy)carbonyl,     (C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl, (C₃-C₆-cycloalkyl)carbonyl;     (C₁-C₄-haloalkyl)carbonyl, (C₁-C₄-haloalkoxy)carbonyl,     (halo-C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl,     (C₃-C₆-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,     chlorine and/or bromine atoms: or —C(═O)C(═O)R⁶, —CONR⁷R⁸ or     —CH₂NR⁹R¹⁰. -   R¹ particularly preferably represents hydrogen, methyl, ethyl, n- or     isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,     methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-,     sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or     isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl,     methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,     cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,     trifluoroethyl, difluoromethylthio, difluorochloromethylthio,     trifluoromethylthio, trifluoromethylsulphinyl,     trifluoromethylsulphonyl, trifluoromethoxymethyl; formyl, —CH₂—CHO,     —(CH₂)₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂,     —(CH₂)₂—CO—CH₃, —(CH₂)₂—CO—CH₂CH₃, —(CH₂)₂—CO—CH(CH₃)₂, —CH₂—CO₂CH₃,     —CH₂—CO₂CH₂CH₃, —CH₂—CO₂CH(CH₃)₂, —(CH₂)₂CO₂CH₃, —(CH₂)₂—CO₂CH₂CH₃,     —(CH₂)₂—CO₂CH(CH₃)₂, —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃,     —CH₂—CO—CH₂CCl₃, —(CH₂)₂—CO—CH₂CF₃, —(CH₂)₂—CO—CH₂CCl₃,     —CH₂—CO₂CH₂CF₃, —CH₂—CO₂CF₂CF₃, —CH₂—CO₂CH₂CCl₃, —CH₂—CO₂CCl₂CCl₃,     —(CH₂)₂—CO₂CH₂—CF₃, —(CH₂)₂—CO₂CH₂CCl₃, —(CH₂)₂—CO₂CCl₂CCl₃;     methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl,     tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl,     tert-butoxycarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl,     trifluoromethoxycarbonyl, or —C(═O)C(═O)R⁶, —CONR⁷R⁸ or —CH₂NR⁹R¹⁰. -   R¹ very particularly preferably represents hydrogen, methyl,     methoxymethyl, formyl, —CH₂—CHO, —(CH₂)₂—CHO, —CH₂—CO—CH₃,     —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂, —C(═O)CHO, —C(═O)C(═O)CH₃,     —C(═O)C(═O)CH₂OCH₃, —C(═O)CO₂CH₃, —C(═O)CO₂CH₂CH₃. -   L preferably represents L¹. -   L¹ preferably represents one of the groups below

-    in which     -   m represents 0, 1 or 2,     -   n represents 0, 1, 2, 3, or 4,     -   Y¹ represents fluorine, chlorine, methyl, ethyl, n- or         isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or         difluoromethyl, where the radicals Y¹ may be identical or         different if m or n is greater than 1. -   L¹ particularly preferably represents one of the groups below

-    in which     -   m represents 0, 1 or 2,     -   n represents 0, 1, 2, 3, or 4,     -   Y¹ represents fluorine, chlorine, methyl, ethyl, n- or         isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or         difluoromethyl, where the radicals Y¹ may be identical or         different if m or n is greater than 1. -   L furthermore preferably represents L². -   L² preferably represents cyclohexenylene (cyclohexenediyl) which is     optionally mono- to tetra-substituted by identical or different     substituents from the group consisting of fluorine, chlorine,     methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,     trifluoromethyl and difluoromethyl and where the double bond may be     in the 1,2-position, 2,3-position, 3,4-position, 4,5-position or     5,6-position. -   L² particularly preferably represents the group

-    in which     -   r represents 0 or 1,     -   Y² represents fluorine, chlorine or methyl. -   R² preferably represents hydrogen, fluorine, chlorine, methyl,     ethyl, n- or isopropyl, or represents methyl, ethyl, n- or     isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or     polysubstituted by identical or different substituents from the     group consisting of fluorine, chlorine and bromine. -   R¹ particularly preferably represents hydrogen, fluorine, chlorine,     methyl, ethyl, trifluoromethyl, difluoromethyl, fluoromethyl,     trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl,     fluorodichloromethyl, difluorochloromethyl, pentafluoroethyl,     1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl     2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,     2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl,     2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or     heptafluoro-isopropyl. -   R² very particularly preferably represents hydrogen, methyl, ethyl     or trifluoromethyl. -   R² especially preferably represents hydrogen or methyl. -   R³ preferably represents fluorine, chlorine, bromine, methyl, ethyl,     n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl,     ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which     is mono- or polysubstituted by identical or different substituents     from the group consisting of fluorine, chlorine and bromine. -   R³ particularly preferably represents fluorine, chlorine, methyl,     ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,     trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl,     dichloromethyl, chloromethyl, chlorofluoromethyl,     fluorodichloromethyl, difluorochloromethyl, pentafluoroethyl,     1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,     2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,     2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl,     2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl,     heptafluoro-n-propyl or heptafluoroisopropyl. -   R³ very particularly preferably represents chlorine, methyl, ethyl,     isopropyl or trifluoromethyl. -   R⁴ preferably represents fluorine, chlorine, bromine, methyl, ethyl,     n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl,     ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which     is mono- or polysubstituted by identical or different substituents     from the group consisting of fluorine, chlorine and bromine. -   R⁴ particularly preferably represents fluorine, chlorine, methyl,     ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,     trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl,     dichloromethyl, chloromethyl, chlorofluoromethyl,     fluorodichloromethyl, difluorochloromethyl, pentafluoroethyl,     1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,     2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,     2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl,     2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or     heptafluoroisopropyl. -   R⁴ very particularly preferably represents chlorine, methyl, ethyl,     isopropyl or trifluoromethyl. -   R⁵ preferably represents hydrogen, fluorine, chlorine, bromine,     methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or     represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or     tert-butyl, each of which is mono- or polysubstituted by identical     or different substituents from the group consisting of fluorine,     chlorine and bromine. -   R⁵ particularly preferably represents hydrogen, fluorine, chlorine,     methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,     trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl,     dichloromethyl, chloromethyl, chlorofluoromethyl,     fluorodichloromethyl, difluorochloromethyl, pentafluoroethyl,     1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,     2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,     2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl,     2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or     heptafluoroisopropyl. -   R⁵ very particularly preferably represents hydrogen, chlorine,     methyl, ethyl, isopropyl or trifluoromethyl. -   R³ and R⁴ furthermore preferably together with the carbon atom to     which they are attached form a 3- to 6-membered carbocyclic or     heterocyclic saturated or unsaturated ring which is optionally     substituted by halogen, methyl, ethyl, methoxy, trifluoromethyl or     trifluoromethoxy, -   R³ and R⁴ furthermore very particularly preferably together with the     carbon atom to which they are attached form a 3-, 5- or 6-membered     carbocyclic saturated ring which is optionally substituted by     methyl, ethyl or trifluoromethyl, -   R³ and R⁴ furthermore very particularly preferably together with the     carbon atom to which they are attached form a 6-membered carbocyclic     unsaturated ring which is optionally substituted by halogen, methyl,     ethyl, methoxy, trifluoromethyl or trifluoromethoxy. -   R⁴⁹ and R⁵⁰ independently of one another preferably represent     C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₃-alkoxy-C₁-C₃-alkyl or     C₁-C₃-alkylthio-C₁-C₃-alkyl. -   R⁴⁹ and R⁵⁰ independently of one another particularly preferably     represent methyl, ethyl, methoxy, ethoxy, methoxymethyl,     ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl,     ethylthiomethyl, methylthioethyl or ethylthioethyl. -   R⁴⁹ and R⁵⁰ independently of one another very particularly     preferably represent methyl, methoxy, methoxymethyl or     methylthiomethyl. -   R⁴⁹ and R⁵⁰ especially preferably each represent methyl. -   R⁵¹ preferably represents C₁-C₆-alkyl, C₁-C₆-alkoxy,     C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁-C₃-alkylthio-C₁-C₃-alkyl,     C₃-C₆-cycloalkyl, phenyl or benzyl. -   R⁵¹ particularly preferably represents methyl, ethyl, n- or     isopropyl, n-, sec-, iso- or tert-butyl, methoxy, ethoxy, n- or     isopropoxy, n-, sec-, iso- or tert-butoxy, methoxymethyl,     ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl,     ethylthiomethyl, methylthioethyl, ethylthioethyl, cyclopropyl,     phenyl or benzyl. -   R⁵¹ very particularly preferably represents methyl, ethyl, n- or     isopropyl, iso- or tert-butyl, methoxy, isopropoxy, iso- or     tert-butoxy, methoxymethyl, methylthiomethyl or phenyl. -   R⁵¹ especially preferably represents methyl, ethyl, n- or isopropyl,     iso- or tert-butyl, methoxy, isopropoxy, iso- or tert-butoxy. -   R⁵¹ most preferably represents methyl. -   R⁶ preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₄-alkoxy,     C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁-C₆-cycloalkyl; C₁-C₄-haloalkyl,     C₁-C₄-haloalkoxy, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,     C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine     and/or bromine atoms. -   R⁶ particularly preferably represents hydrogen, methyl, ethyl, n- or     isopropyl, tert-butyl, methoxy, ethoxy, n- or isopropoxy,     tert-butoxy, methoxymethyl, cyclopropyl; trifluoromethyl,     trifluoromethoxy. -   R⁷ and R⁸ independently of one another preferably represent     hydrogen, C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl;     C₁-C₄-haloalkyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-halocycloalkyl     having in each case 1 to 9 fluorine, chlorine and/or bromine atoms. -   R⁷ and R⁸ furthermore together with the nitrogen atom to which they     are attached preferably form a saturated heterocycle which is     optionally mono- to tetrasubstituted by identical or different     substituents from the group consisting of halogen and C₁-C₄-alkyl     and which has 5 or 6 ring atoms, where the heterocycle may contain 1     or 2 further non-adjacent heteroatoms from the group consisting of     oxygen, sulphur and NR¹¹. -   R⁷ and R⁸ independently of one another particularly preferably     represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-     or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,     ethoxyethyl, cyclopropyl cyclopentyl, cyclohexyl; trifluoromethyl,     trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. -   R⁷ and R⁸ furthermore together with the nitrogen atom to which they     are attached particularly preferably form a saturated heterocycle     from the group consisting of morpholine, thiomorpholine and     piperazine which is optionally mono- to tetrasubstituted by     identical or different substituents from the group consisting of     fluorine, chlorine, bromine and methyl, where the piperazine may be     substituted at the second nitrogen atom by R¹¹. -   R⁹ and R¹⁰ independently of one another preferably represent     hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,     C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine     and/or bromine atoms. -   R⁹ and R¹⁰ furthermore together with the nitrogen atom to which they     are attached preferably form a saturated heterocycle which is     optionally mono- or polysubstituted by identical or different     substituents from the group consisting of halogen and C₁-C₄-alkyl     and which has 5 or 6 ring atoms, where the heterocycle may contain 1     or 2 further non-adjacent heteroatoms from the group consisting of     oxygen, sulphur and NR¹¹. -   R⁹ and R¹⁰ independently of one another particularly preferably     represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-     or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,     ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl,     trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. -   R⁹ and R¹⁰ furthermore together with the nitrogen atom to which they     are attached particularly preferably form a saturated heterocycle     from the group consisting of morpholine, thiomorpholine and     piperazine which is optionally mono- to tetrasubstituted by     identical or different substituents from the group consisting of     fluorine, chlorine, bromine and methyl, where the piperazine may be     substituted at the second nitrogen atom by R¹¹. -   R¹¹ preferably represents hydrogen or C₁-C₄-alkyl. -   R¹¹ particularly preferably represents hydrogen, methyl, ethyl, n-     or isopropyl, n-, iso-, sec- or tert-butyl. -   A preferably represents one of the radicals A1, A2, A3, A4, A5, A6,     A9, A10, A11, A12, A16, A17 or A18. -   A particularly preferably represents one of the radicals A1, A2, A3,     A4, A5, A6, A9, A11, A16, A17, A18. -   A very particularly preferably represents the radical A1. -   A furthermore very particularly preferably represents the radical     A2. -   A furthermore very particularly preferably represents the radical     A3. -   A furthermore very particularly preferably represents the radical     A4. -   A furthermore very particularly preferably represents the radical     A5. -   A furthermore very particularly preferably represents the radical     A6. -   A furthermore very particularly preferably represents the radical     A9. -   A furthermore very particularly preferably represents the radical     A11. -   A furthermore very particularly preferably represents the radical     A16. -   A furthermore very particularly preferably represents the radical     A17. -   A furthermore very particularly preferably represents the radical     A18. -   R¹² preferably represents hydrogen, cyano, fluorine, chlorine,     bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy,     methylthio, ethylthio, cyclopropyl, C₁-C₂-haloalkyl,     C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine     and/or bromine atoms, trifluoromethylthio, difluoromethylthio,     aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl. -   R¹² particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl,     monofluoroethyl, difluoromethyl, trifluoromethyl,     difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl,     methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio,     ethylthio, trifluoromethylthio or difluoromethylthio. -   R¹² very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl,     monofluoroethyl, difluoromethyl, trifluoromethyl,     difluorochloromethyl or trichloromethyl. -   R¹³ especially preferably represents methyl, difluoromethyl,     trifluoromethyl or 1-fluoroethyl. -   R¹³ preferably represents hydrogen, fluorine, chlorine, bromine,     iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio. -   R¹³ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine or methyl. -   R¹³ very particularly preferably represents hydrogen, fluorine,     chlorine or methyl. -   R¹⁴ preferably represents hydrogen, methyl, ethyl, n-propyl,     isopropyl, C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or     bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,     cyclopentyl, cyclohexyl or phenyl. -   R¹⁴ particularly preferably represents hydrogen, methyl, ethyl,     isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl,     hydroxyethyl or phenyl. -   R¹⁴ very particularly preferably presents hydrogen, methyl,     trifluoromethyl or phenyl. -   R¹⁴ especially preferably represents methyl. -   R¹⁵ and R¹⁶ independently of one another preferably represent     hydrogen, fluorine, chlorine, bromine, methyl, ethyl or     C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R¹⁵ and R¹⁶ independently of one another particularly preferably     represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,     difluoromethyl, trifluoromethyl, difluorochloromethyl or     trichloromethyl. -   R¹⁵ and R¹⁶ independently of one another very particularly     preferably represent hydrogen, fluorine, chlorine, bromine, methyl,     ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. -   R¹⁵ and R¹⁶ especially preferably each represent hydrogen. -   R¹⁷ preferably represents fluorine, chlorine, bromine, cyano,     methyl, ethyl, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy having in each     case 1 to 5 fluorine, chlorine and/or bromine atoms. -   R¹⁷ particularly preferably represents fluorine, chlorine, bromine,     cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy,     difluorochloromethoxy or trichloromethoxy. -   R¹⁷ very particularly preferably represents fluorine, chlorine,     bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy. -   R¹⁷ especially preferably represents methyl. -   R¹⁸ and R¹⁹ independently of one another preferably represent     hydrogen, fluorine, chlorine, bromine, methyl, ethyl or     C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R¹⁸ and R¹⁹ independently of one another particularly preferably     represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,     difluoromethyl, trifluoromethyl, difluorochloromethyl or     trichloromethyl. -   R¹⁸ and R¹⁹ independently of one another very particularly     preferably represent hydrogen, fluorine, chlorine, bromine, methyl,     ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. -   R¹⁸ and R¹⁹ especially preferably each represent hydrogen. -   R²⁰ preferably represents hydrogen, fluorine, chlorine, bromine,     methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine     and/or bromine atoms. -   R²⁰ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, methyl or trifluoromethyl. -   R²⁰ very particularly preferably represents methyl. -   R²¹ preferably represents hydrogen, fluorine, chlorine, bromine,     iodine, hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl,     C₁-C₂-haloalkoxy or C₁-C₂-haloalkylthio having in each case 1 to 5     fluorine, chlorine and/or bromine atoms. -   R²¹ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl,     isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl,     trifluoromethyl, difluorochloromethyl, trichloromethyl,     trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,     trichloromethoxy, trifluoromethylthio, difluoromethylthio,     difluorochloromethylthio or trichloromethylthio. -   R²¹ very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl     or trichloromethyl. -   R²¹ especially preferably represents iodine, methyl, difluoromethyl     or trifluoromethyl. -   R²² preferably represents fluorine, chlorine, bromine, iodine,     hydroxyl, cyano, C₁-C₄-alkyl, methoxy, ethoxy, methylthio,     ethylthio, difluoromethylthio, trifluoromethylthio, C₁-C₂-haloalkyl     or C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine     and/or bromine atoms. -   R²² particularly preferably represents fluorine, chlorine, bromine,     iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl,     n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl,     difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy,     ethoxy, methylthio, ethylthio, difluoromethylthio,     trifluoromethylthio, trifluoromethoxy, difluoromethoxy,     difluorochloromethoxy or trichloromethoxy. -   R²² very particularly preferably represents fluorine, chlorine,     bromine, iodine, methyl, trifluoromethyl, difluoromethyl or     trichloromethyl. -   R²³ preferably represents hydrogen, fluorine, chlorine, bromine,     iodine, cyano, C₁-C₄-alkyl, methoxy, ethoxy, methylthio, ethylthio,     C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy having in each case 1 to 5     fluorine, chlorine and/or bromine atoms, C₁-C₂-alkylsulphinyl or     C₁-C₂-alkylsulphonyl. -   R²³ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl,     sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,     difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio,     ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,     trichloromethoxy, methylsulphinyl or methylsulphonyl. -   R²³ very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl,     sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,     trichloromethyl, methylsulphinyl or methylsulphonyl. -   R²³ especially preferably represents hydrogen. -   R²⁴ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1     to 5 fluorine, chlorine and/or bromine atoms. -   R²⁴ particularly preferably represents methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R²⁵ preferably represents methyl or ethyl. -   R²⁵ particularly preferably represents methyl. -   Q¹ preferably represents S (sulphur), SO₂ or CH₂. -   Q¹ particularly preferably represents S (sulphur) or CH₂. -   Q¹ very particularly preferably represents S (sulphur). -   p preferably represents 0 or 1. -   p particularly preferably represents 0. -   R²⁶ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1     to 5 fluorine, chlorine and/or bromine atoms. -   R²⁶ particularly preferably represents methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R²⁶ very particularly preferably represents methyl, trifluoromethyl,     difluoromethyl or trichloromethyl. -   R²⁷ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1     to 5 fluorine, chlorine and/or bromine atoms. -   R²⁷ particularly preferably represents methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R²⁷ very particularly preferably represents methyl, trifluoromethyl,     difluoromethyl or Trichloromethyl. -   R²⁸ and R²⁹ independently of one another preferably represent     hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or     C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R²⁸ and R²⁹ independently of one another particularly preferably     represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R²⁸ and R²⁹ independently of one another very particularly     preferably represent hydrogen, fluorine, chlorine, bromine, methyl,     trifluoromethyl, difluoromethyl or trichloromethyl. -   R²⁸ and R²⁹ especially preferably each represent hydrogen. -   R³⁰ preferably represents hydrogen, fluorine, chlorine, bromine,     iodine, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,     chlorine and/or bromine atoms. -   R³⁰ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl,     difluorochloromethyl or trichloromethyl. -   R³⁰ very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or     trichloromethyl. -   R³⁰ especially preferably represents methyl. -   R³¹ and R³² independently of one another preferably represent     hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl     or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R³¹ and R³² independently of one another particularly preferably     represent hydrogen, fluorine, chlorine, bromine, nitro, methyl,     ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R³¹ and R³² independently of one another very particularly     preferably represent hydrogen, fluorine, chlorine, bromine, methyl,     trifluoromethyl, difluoromethyl or trichloromethyl. -   R³¹ and R³² especially preferably each represent hydrogen. -   R³³ preferably represents hydrogen, fluorine, chlorine, bromine,     iodine, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,     chlorine and/or bromine atoms. -   R³³ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl,     difluorochloromethyl or trichloromethyl. -   R³³ very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or     trichloromethyl. -   R³³ especially preferably represents methyl. -   R³⁴ preferably represents hydrogen, fluorine, chlorine, bromine,     amino, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl     or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R³⁴ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R³⁴ very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, amino, methylamino, dimethylamino, methyl,     trifluoromethyl, difluoromethyl or trichloromethyl. -   R³⁴ especially preferably represents amino, methylamino,     dimethylamino, methyl or trifluoromethyl. -   R³⁵ preferably represents fluorine, chlorine, bromine, methyl, ethyl     or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R³⁵ particularly preferably represents fluorine, chlorine, bromine,     methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl     or trichloromethyl. -   R³⁵ very particularly preferably represents fluorine, chlorine,     bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. -   R³⁵ especially preferably represents methyl, trifluoromethyl or     difluoromethyl. -   R³⁶ preferably represents hydrogen, fluorine, chlorine, bromine,     amino, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl     or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R³⁶ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R³⁶ very particularly preferably represents hydrogen, fluorine,     chlorine, bromine, amino, methylamino, dimethylamino, methyl,     trifluoromethyl, difluoromethyl or trichloromethyl. -   R³⁶ especially preferably represents amino, methylamino,     dimethylamino, methyl or trifluoromethyl. -   R³⁷ preferably represents fluorine, chlorine, bromine, methyl, ethyl     or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R³⁷ particularly preferably represents fluorine, chlorine, bromine,     methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl     or trichloromethyl. -   R³⁷ very particularly preferably represents fluorine, chlorine,     bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. -   R³⁷ especially preferably represents methyl, trifluoromethyl or     difluoromethyl. -   R³⁸ preferably represents fluorine, chlorine, bromine, methyl, ethyl     or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine     atoms. -   R³⁸ particularly preferably represents fluorine, chlorine, bromine,     methyl, ethyl, trifluoromethyl, Difluoromethyl, difluorochloromethyl     or trichloromethyl. -   R³⁸ very particularly preferably represents fluorine, chlorine,     bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. -   R³⁹ preferably represents hydrogen, methyl or ethyl. -   R³⁹ particularly preferably represents methyl. -   R⁴⁰ preferably represents fluorine, chlorine, bromine, methyl or     ethyl. -   R⁴⁰ particularly preferably represents fluorine, chlorine or methyl. -   R⁴¹ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1     to 5 fluorine, chlorine and/or bromine atoms. -   R⁴¹ particularly preferably represents methyl, ethyl,     trifluoromethyl, difluoromethyl, difluorochloromethyl or     trichloromethyl. -   R⁴¹ very particularly preferably represents methyl, trifluoromethyl,     difluoromethyl or trichloromethyl. -   R⁴¹ especially preferably represents methyl or trifluoromethyl. -   R⁴² preferably represents hydrogen, fluorine, chlorine, bromine,     methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine     and/or bromine atoms. -   R⁴² particularly preferably represents hydrogen, fluorine, chlorine,     bromine, methyl or trifluoromethyl. -   R⁴³ preferably represents fluorine, chlorine, bromine, iodine,     hydroxyl, C₁-C₄-alkyl, methoxy, ethoxy, methylthio, ethylthio,     difluoromethylthio, trifluoromethylthio, C₁-C₂-haloalkyl or     C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine     and/or bromine atoms. -   R⁴³ particularly preferably represents fluorine, chlorine, bromine,     iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,     sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,     difluorochloromethyl or trichloromethyl. -   R⁴³ very particularly preferably represents fluorine, chlorine,     bromine, iodine, methyl, trifluoromethyl, difluoromethyl or     trichloromethyl. -   R⁴⁴ preferably represents hydrogen, methyl, ethyl, C₁-C₂-haloalkyl     having 1 to 5 fluorine, chlorine and/or bromine atoms,     C₁-C₂-alkoxy-C₁-C₂-alkyl, hydroxymethyl, hydroxyethyl,     methylsulphonyl or dimethylaminosulphonyl. -   R⁴⁴ particularly preferably represents hydrogen, methyl, ethyl,     trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or     hydroxyethyl. -   R⁴⁴ very particularly preferably represents methyl or methoxymethyl. -   R⁴⁵ preferably represents hydrogen, fluorine, chlorine, bromine,     methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine     and/or bromine atoms. -   R⁴⁵ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or     trichloromethyl. -   R⁴⁵ very particularly preferably represents hydrogen or methyl. -   R⁴⁶ preferably represents hydrogen, fluorine, chlorine, bromine,     iodine, cyano, methyl, ethyl, isopropyl or C₁-C₂-haloalkyl having 1     to 5 fluorine, chlorine and/or bromine atoms. -   R⁴⁶ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, cyano, methyl, ethyl, isopropyl, trifluoromethyl,     difluoromethyl, difluorochloromethyl or trichloromethyl. -   R⁴⁶ very particularly preferably represents hydrogen, methyl,     difluoromethyl or trifluoromethyl. -   R⁴⁷ preferably represents hydrogen, fluorine, chlorine, bromine,     methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine     and/or bromine atoms. -   R⁴⁷ particularly preferably represents hydrogen, fluorine, chlorine,     bromine, iodine, methyl or trifluoromethyl. -   R⁴⁷ very particularly preferably represents hydrogen. -   R⁴⁸ preferably represents methyl, ethyl, n-propyl or isopropyl. -   R⁴⁸ particularly preferably represents methyl or ethyl.

Preference is given to those compounds of the formula (I) in which all radicals each have the meanings mentioned above as being preferred.

Particular preference is given to those compounds of the formula (I) in which all radicals each have the meanings mentioned above as being particularly preferred.

Very particular preference is given to those compounds of the formula (I) in which all radicals each have the meanings mentioned above as being very particularly preferred.

Preferred, and in each case to be understood as a sub-group of tire compounds of the formula (I) mentioned above, are the following groups of novel carboxamides:

-   Group 1: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-g)

in which s, L, R², R³, R⁴, R⁵ and A are as defined above.

-   Group 2: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-b)

in which s, R^(1A), L, R², R³, R⁴, R⁵ and A are as defined above.

-   R^(1A) preferably represents C₁-C₆-alkyl, C₁-C₄-alkylsulphinyl,     C₁-C₄-alkylsulphonyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl;     C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,     C₁-C₄-haloalkylsulphonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,     C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine     and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,     (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,     (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;     halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,     halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13     fluorine, chlorine and/or bromine atoms; -    (C₁-C₆-alkyl)carbonyl, (C₁-C₄-alkoxy)carbonyl,     (C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl, (C₃-C₆-cycloalkyl)carbonyl;     (C₁-C₄-haloalkyl)carbonyl, (C₁-C₄-haloalkoxy)carbonyl,     (halo-C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl,     (C₃-C₆-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,     chlorine and/or bromine atoms; or —C(═O)C(═O)R⁶, —CONR⁷R⁸ or     —CH₂NR⁹R¹⁰. -   R^(1A) particularly preferably represents methyl, ethyl, n- or     isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,     methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-,     sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or     isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl,     methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,     cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,     trifluoroethyl, difluoromethylthio, difluorochloromethylthio,     trifluoromethylthio, trifluoromethylsulphinyl,     trifluoromethylsulphonyl, trifluoromethoxymethyl; formyl, —CH₂—CHO,     —(CH₂)₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂,     —(CH₂)₂—CO—CH₃, —(CH₂)₂—CO—CH₂CH₃, —(CH₂)₂CO—CH(CH₃)₂, —CH₂—CO₂CH₃,     —CH₂—CO₂CH₂CH₃, —CH₂—CO₂CH(CH₃)₂, —(CH₂)₂—CO₂CH₃, —(CH₂)₂—CO₂CH₂CH₃,     —(CH₂)₂—CO₂CH(CH₃)₂, —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃,     —CH₂—CO—CH₂CCl₃, —(CH₃)₂CO—CH₂CF₃, —(CH₂)₂—CO—CH₂CCl₃,     —CH₂—CO₂CH₂CF₃, —CH₂—CO₂CF₂CF₃, —CH₂—CO₂CH₂CCl₃, —CH₂—CO₂CCl₂CCl₃,     —(CH₂)₂—CO₂CH₂CF₃, —(CH₂)₂—CO₂CF₂CF₃, —(CH₂)₂—CO₂CH₂CCl₃,     —(CH₂)₂—CO₂CCl₂CCl₃; methylcarbonyl, ethylcarbonyl,     n-propylcarbonyl, isopropylcarbonyl, tert-butylcarbonyl,     methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl,     cyclopropylcarbonyl; trifluoromethylcarbonyl,     trifluoromethoxycarbonyl, or —C(═O)C(═O)R⁶, —CONR⁷R⁸ or —CH₂NR⁹R¹⁰. -   R^(1A) very particularly preferably represents methyl,     methoxymethyl, formyl, —CH₂—CHO, —(CH₂)₂—CHO, —CH₂—CO—CH₃,     —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂, —C(═O)CHO, —C(═O)C(═O)CH₃,     —C(═O)C(═O)CH₂OCH₃, —C(═O)CO₂CH₃, —C(═O)CO₂CH₂CH₃. -   Group 3: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-c)

in which s, R¹, R², R³, R⁴, R⁵, A, Y¹ and n are as defined above.

Emphasis is given to compounds of the formula (I-c), in which n represents 0.

Emphasis is given to compounds of the formula (I-c), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-c), in which s represents 1.

-   Group 4: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-d)

in which s, R¹, R², R³, R⁴, R⁵, A, Y¹ and n are as defined above.

Emphasis is given to compounds of the formula (I-d), in which n represents 0.

Emphasis is given to compounds of the formula (I-d), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-d), in which s represents 1.

-   Group 5: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-e)

in which s, R¹, R², R³, R⁴, R⁵, A, Y¹ and m are as defined above.

Emphasis is given to compounds of the formula (I-e), in which m represents 0.

Emphasis is given to compounds of the formula (I-e), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-e), in which s represents 1.

-   Group 6: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-f)

in which s, R¹, R², R³, R⁴, R⁵, A, Y² and r are as defined above.

Emphasis is given to compounds of the formula (I-f), in which r represents 0.

Emphasis is given to compounds of the formula (I-f), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-f), in which s represents 1.

-   Group 7: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-h)

in which s, L, R², R⁴⁹, R⁵⁰, R⁵¹ and A are as defined above.

-   Group 8: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-i)

in which s, R^(1A), L, R², R⁴⁹, R⁵⁰, R⁵¹ and A are as defined above.

-   Group 9: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-k)

in which s, R¹, R², R⁴⁹, R⁵⁰, R⁵¹, A, Y¹ and n are as defined above.

Emphasis is given to compounds of the formula (I-k), in which n represents 0.

Emphasis is given to compounds of the formula (I-k), in winch R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-k), in which s represents 1.

-   Group 10: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-l)

in which s, R¹, R², R⁴⁹, R⁵⁰, R⁵¹, A, Y¹ and n are as defined above.

Emphasis is given to compounds of the formula (I-l), in which n represents 0.

Emphasis is given to compounds of the formula (I-l), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-l), in which s represents 1.

-   Group 11: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-m)

in which s, R¹, R², R⁴⁹, R⁵⁰, R⁵¹, A, Y¹ and m are as defined above.

Emphasis is given to compounds of the formula (I-m), in which m represents 0.

Emphasis is given to compounds of the formula (I-m), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-m), in which s represents 1.

-   Group 12: 2-alkylcycloalk(en)ylcarboxamides of the formula (I-n)

in which s, R¹, R², R⁴⁹, R⁵⁰, R⁵¹, A, Y² and r are as defined above.

Emphasis is given to compounds of the formula (I-n), in which r represents 0.

Emphasis is given to compounds of the formula (I-n), in which R¹ represents hydrogen.

Emphasis is given to compounds of the formula (I-n), in which s represents 1.

Emphasis is given to compounds of the formula (I) (and also of groups 2 to 6 and 8 to 12), in which R¹ or R^(1A) represents formyl.

Emphasis is furthermore given to compounds of the formula (I) (and also of groups 2 to 6 and 8 to 12), in which R¹ or R^(1A) represents —C(═O)C(═O)R⁶, where R⁶ is as defined above.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy.

Optionally substituted radicals may be mono- or polysubstituted, where in the case of polysubstitution the substituents may be identical or different. Thus, the definition dialkylamino also embraces an amino group which is substituted asymmetrically by alkyl, such as, for example, methylethylamino.

Halogen-substituted radicals, such as, for example, haloalkyl, are mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms may be identical or different. Here, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

The general or preferred radical definitions or illustrations given above can be combined as desired between the respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates. In particular, the compounds mentioned in groups 1 to 6 may be combined both with the general and with the preferred, particularly preferred, etc., meanings, here, too, any combinations between the preferred ranges being possible.

DESCRIPTION OF THE PROCESSES ACCORDING TO THE INVENTION FOR PREPARING THE 2-alkylcycloalk(en)ylcarboxamides OF THE FORMULA (I) AND THE INTERMEDIATES Process (a)

Using 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and 2-(1,3-dimethylbutyl)-cyclohexanamine as starting material, the process (a) according to the invention can be illustrated by the formula scheme below:

The formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process (a) according to the invention. In this formula (II), A preferably, particularly preferably or very particularly preferably has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for this radical. X¹ preferably represents chlorine, bromine or hydroxyl.

The carboxylic acid derivatives of the formula (II) are known and/or can be prepared by known processes (cf. WO 03/066609, WO 03/066610, EP-A 0 545 099, EP-A 0 589 301, EP-A 0 589 313 and U.S. Pat. No. 3,547,917).

The formula (III) provides a general definition of the aniline derivatives furthermore required as starting materials for carrying out the process (a) according to the invention. In this formula (III), X, s, R¹, L and R² preferably, particularly preferably or very particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals or this index.

Some of the aniline derivatives of the formula (III) are already known, or they can be obtained by known processes (cf, for example, EP-A 0 589 313).

It is also possible to prepare initially aniline derivatives of the formula (III-a)

in which X, s, L and R² are as defined above and to react these, if appropriate, subsequently with halides of the formula (IV) R^(1A)—X²  (IV) in which R^(3A) and X⁴ are as defined above, in the presence of a base and in the presence of a diluent. [The reaction conditions of the process (b) according to the invention apply correspondingly.]

Aniline derivatives of the formula (III) are also obtained when

-   (c) cyclic ketones of the formula (V)

-    in which     -   L^(1a) represents C₂-C₆-alkylene (C₂-C₆-alkanediyl) which is         optionally mono- to tetra-substituted by identical or different         substituents from the group consisting of fluorine, chlorine,         C₁-C₄-alkyl or C₁-C₄-haloalkyl, -    are initially reacted with carbonyl compounds of the formula (VI)

-    in which X, s and R² are as defined above, -    in the presence of a base to give the compounds of the formulae     (VIIa) and (VIIb)

-    in which -    X, S and R² are as defined above and     -   L^(1b) represents C₁-C₅-alkylene (C₁-C₅-alkanediyl) which is         optionally mono- to tetra-substituted by identical or different         substituents from the group consisting of fluorine, chlorine,         C₁-C₄-alkyl and C₁-C₄-haloalkyl, -    and these are then subjected to a reductive amination by customary     methods.

The formula (V) provides a general definition of the cyclic ketones required as starting materials for carrying out the process (c) according to the invention. In this formula (V), L^(1a) preferably represents —(CH₂)₂— which is optionally substituted m times by Y¹ or represents —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₆—, each of which is optionally substituted n times by Y¹, where m, n and Y¹ are as defined above. L^(1a) particularly preferably represents —(CH₂)₂— which is optionally substituted m times by Y¹ or represents —(CH₂)₄— or —(CH₂)₅— which are each optionally substituted n times by Y¹, where m, n and Y¹ are as defined above.

The formula (VI) provides a general definition of the carbonyl compounds furthermore required as starting materials for carrying out the process (c) according to the invention. In this formula (VI), X, s and R² preferably, particularly preferably and very particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals.

The formulae (VIIa) and (VIIb) provide general definitions of the compounds formed as intermediates when carrying out the process (c) according to the invention. In these formulae (VIIa) and (VIIb) L^(1b) preferably represents —(CH₂)— which is optionally substituted m times by Y¹ or represents —(CH₂)₂—, —(CH₂)₃—, —(CH₂)₄— or —(CH₂)₅—, each of which is optionally substituted n times by Y¹, where m, n and Y¹ are as defined above. L^(1b) particularly preferably represents —(CH₂)— which is optionally substituted m times by Y¹ or represents —(CH₂)₃— or —(CH₂)₄—, each of which is optionally substituted n times by Y¹, where m, n and Y¹ are as defined above. X, s and R² preferably, particularly preferably or very particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals.

Cyclic ketones of the formula (V) and carbonyl compounds of the formula (VI) are known or can be prepared by processes known from the literature (Organic Letters 2001, Vol. 3, 573; Tetrahedron Letters 42 (2001) 4257).

Process (b)

Using N-[2-(1,3-dimethylbutyl)cyclohexyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide and acetyl chloride as starting materials, the course of the process (b) according to the invention can be illustrated by the formula scheme below:

The formula (I-a) provides a general definition of the 2-alkylcycloalk(en)ylcarboxamides required as starting materials for carrying out the process (b) according to the invention. In this formula (I-a), X, s, L, R² and A preferably, particularly preferably or very particularly preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred, particularly preferred and very particularly preferred, respectively, for these radicals.

The compounds of the formula (I-a) are compounds according to the invention and can be prepared by process (a).

The formula (IV) provides a general definition of the halides furthermore required as starting materials for carrying out the process (b) according to the invention. In this formula (IV), R^(1A) preferably, particularly preferably or very particularly preferably has those meanings which have already been mentioned above for the compounds of the formula (I-b) as being preferred, particularly preferred and very particularly preferred, respectively, for this radical. X⁴ represents chlorine, bromine or iodine.

Halides of the formula (IV) are known.

Reaction Conditions

Suitable diluents for carrying out the process (a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl iso-butyl ketone or cyclohexanone; nitriles, such as acetonitrile, propionitrile, n- or isobutyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimetylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; mixtures thereof with water or pure water.

The process (a) according to the invention is, if appropriate, carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The process (a) according to the invention is, if appropriate, carried out in the presence of a suitable condensing agent. Suitable condensing agents are all condensing agents usually used for such amidation reactions. By way of example, mention may be made of acid halide formers, such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; anhydride formers, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulphonyl chloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC), or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N,N′-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/carbon tetrachloride or bromotripyrrolidinophosphonium hexafluorophosphate.

The process (a) according to the invention is, if appropriate, carried out in the presence of a catalyst. By way of example, mention may be made of 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.

When carrying out the process (a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures of from 0° C. to 150° C., preferably at temperatures from 0° C. to 80° C.

For carrying out the process (a) according to the invention for preparing the compounds of the formula (I), in general from 0.8 to 15 mol, preferably from 0.8 to 8 mol, of aniline derivative of the formula (III) are employed per mole of the carboxylic acid derivative of the formula (II).

Suitable diluents for carrying out the process (b) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

The process (b) according to the invention is carried out in the presence of a base. Suitable bases are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or caesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the process (b) according to the invention, the reaction temperatures can be varied within a relatively large range. In general, the process is carried out at temperatures of from 0° C. to 150° C., preferably at temperatures of from 20° C. to 110° C.

For carrying out the process (b) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of halide of the formula (IV) are employed per mole of the 2-alkylcycloalk(en)ylcarboxamide of the formula (I-a).

Unless indicated otherwise, all processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure—in general between 0.1 bar and 10 bar.

Suitable diluents for carrying out the process (c) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, alcohols, such as, for example, methanol, ethanol, isopropanol, n-, sec- or tert-butanol, mixtures thereof with water or pure water.

The process (c) according to the invention is carried out in the presence of a base. Suitable bases are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or caesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the process (c) according to the invention, the reaction temperatures may be varied within a relatively wide range. In general, the process is carried out at temperatures from −20° C. to 150° C., preferably at temperatures of from 0° C. to 110° C.

For carrying out the process (c) according to the invention for preparing the compounds of the formula (III), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of carbonyl compound of the formula (VI) are employed per mole of the cyclic ketone of the formula (V).

Unless indicated otherwise, all processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure—in general between 0.1 bar and 10 bar.

Process c-2 Reductive Amination

Suitable diluents for carrying out the process (c-2) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexaue, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, alcohols, such as, for example, methanol, ethanol, isopropanol, n-, sec-, or tert-butanol, mixtures thereof with water or pure water.

The reductive amination in the process (c) according to the invention is carried out in the presence of an amine and a reducing agent. Suitable amine components are ammonia, ammonia salts, such as, for example, ammonium formate, but also monosubstituted ammonia, such as, for example, methylamine, ethylamine, propylamine, cyclopropylamine, etc. Suitable reducing agents are all customary inorganic or organic reducing agents. These preferably include alkaline earth metal or alkali metal hydrides, or borohydrides, such as, for example, sodium hydride, sodium cyanoborohydride, sodium borohydride, or sources of hydrogen, such as, for example, elemental hydrogen, hydrazine, cyclohexanediene or formates, or else the formates of the corresponding amine components.

The reductive amination in the process (c) according to the invention is, if appropriate, carried out in the presence of a catalyst. Suitable catalysts are commercial catalysts, such as, for example, hydrogenation catalysts, for example elemental Pd, Ni (or else Raney nickel), Pt, Fe, Ru, Os or salts thereof. These catalysts may be supported on carriers, such as, for example, carbon, silica, zeolites, etc., or be stabilized by ligands.

When carrying out the reductive amination in the process (c) according to the invention, the reaction temperatures may be varied within a relatively wide range. In general, the process is carried out at temperatures from 0° C. to 150° C., preferably at temperatures of from 20° C. to 110° C.

For the reductive amination in the process (c) according to the invention for preparing the compounds of the formula (III), in general from 0.2 to 50 mol, preferably from 1 to 20 mol, of amine and reducing agent, and also 0.01-10 mol % of catalyst are employed per mole of the cyclic ketone of the formula (V).

Unless indicated otherwise, all processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes under elevated or reduced pressure, in general between 0.1 bar and 10 bar.

The substances according to the invention exhibit a potent microbicidal activity and can be employed in plant protection and in the protection of materials for controlling undesirable microorganisms such as fungi and bacteria.

Fungicides can be employed in plant protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides cat be employed in plant protection for combating Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Examples which may be mentioned, but not by limitation, of some pathogens of fungal and bacterial diseases which come under the abovementioned general terms are:

Diseases caused by powdery mildew pathogens, such as, for example

-   Blumeria species such as, for example, Blumeria graminis; -   Podosphaera species such as, for example, Podosphaera leucotricha; -   Sphaerotheca species such as, for example, Sphaerotheca fuliginea; -   Uncinula species such as, for example, Uncinula necator;     diseases caused by rust pathogens such as, for example, -   Gymnosporangium species such as, for example, Gymnosporangium     sabinae -   Hemileia species such as, for example, Hemileia vastatrix; -   Phakopsora species such as, for example, Phakopsora pachyrhizi and     Phakopsora meibomiae: -   Puccinia species such as, for example, Puccinia recondita; -   Uromyces species such as, for example, Uromyces appendiculatus;     diseases caused by pathogens from the Oomycetene group such as, for     example, -   Bremia species such as, for example, Bremia lactucae; -   Peronospora species such as, for example, Peronospora pisi or P.     brassicae; -   Phytophthora species such as, for example, Phytophthora infestans; -   Plasmopara species such as, for example, Plasmopara viticola; -   Pseudoperonospora species such as, for example, Pseudoperonospora     humuli or Pseudoperonospora cubensis; -   Pythium species such as, for example, Pythium ultimum;     leaf spot diseases and leaf wilts caused by, for example, -   Alternaria species such as, for example, Alternaria solani; -   Cercospora species such as, for example, Cercospora beticola; -   Cladiosporum species such as, for example, Cladiosporium     cucumerinum; -   Cochliobolus species such as, for example, Cochliobolus sativus     (conidial form: Drechslera, syn: Helminthosporium); -   Colletotrichum species such as, for example, Colletotrichum     lindemuthanium; -   Cycloconium species such as, for example, Cycloconium oleaginum; -   Diaporthe species such as, for example, Diaporthe citri; -   Elsinoe species such as, for example, Elsinoe fawcettii; -   Gloeosporium species such as, for example, Gloeosporium lacticolor; -   Glomerella species such as, for example, Glomerella cingulata; -   Guignardia species such as, for example, Guignardia bidwelli; -   Leptosphaeria species such as, for example, Leptosphaeria maculans; -   Magnaporthe species such as, for example, Magnaporthe grisea; -   Mycosphaerella species such as, for example, Mycosphaerelle     graminicola; -   Phaeosphaeria species such as, for example, Phaeosphaeria nodorum; -   Pyrenophora species such as, for example, Pyrenophora teres; -   Ramularia species such as, for example, Ramularia collo-cygni; -   Rhynchosporium species such as, for example, Rhynchosporium secalis; -   Septoria species such as, for example, Septoria apii; -   Typhula species such as, for example, Typhula incarnata; -   Venturia species such as, for example, Venturia inaequalis;     root and stem diseases caused by, for example, -   Corticium species such as, for example, Corticium graminearum; -   Fusarium species such as, for example, Fusarium oxysporum; -   Gaeumannomyces species such as, for example, Gaeumannomyces     graminis; -   Rhizoctonia species such as, for example, Rhizoctonia solani; -   Tapesia species such as, for example, Tapesia acuformis; -   Thielaviopsis species such as, for example, Thielaviopsis basicola;     car and panicle diseases (including maize cobs), caused by, for     example, -   Alternaria species such as, for example, Alternaria spp.; -   Aspergillus species such as, for example, Aspergillus flavus; -   Cladosporium species such as, for example, Cladosporium spp.; -   Claviceps species such as, for example, Claviceps purpurea; -   Fusarium species such as, for example, Fusarium culmorum; -   Gibberella species such as, for example, Gibberella zeae; -   Monographella species such as, for example, Monographella nivalis;     diseases caused by smuts such as, for example, -   Sphacelotheca species such as, for example, Sphacelotheca reiliana; -   Tilletia species such as, for example, Tilletia caries; -   Urocystis species such as, for example, Urocystis occulta; -   Ustilago species such as, for example, Ustilago nuda;     fruit rots caused by, for example, -   Aspergillus species such as, for example, Aspergillus flavus; -   Botrytis species such as, for example, Botrytis cinerea; -   Penicillium species such as, for example, Penicillium expansum; -   Sclerotinia species such as, for example, Sclerotinia sclerotiorum; -   Verticilium species such as, for example, Verticilium alboatrum;     seed- and soil-borne rot and wilts, and seedling diseases, caused     by, for example, -   Fusarium species such as, for example, Fusarium culmorum, -   Phytophthora species such as, for example, Phytophthora cactorum; -   Pythium species such as, for example, Pythium ultimum; -   Rhizoctonia species such as, for example, Rhizoctonia solani; -   Sclerotium species such as, for example, Sclerotium rolfsii;     cankers, galls and witches' broom disease, caused by, for example, -   Nectria species such as, for example, Nectria galligena;     Wilts caused by, for example, -   Monilinia species such as, for example, Monilinia laxa;     deformations of leaves, flowers and fruits, caused by, for example, -   Taphrina species such as, for example, Taphrina deformans;     degenerative diseases of woody species, caused by, for example, -   Esca species such as, for example, Phaemoniella clamydospora;     diseases of inflorescences and seeds, caused by, for example, -   Botrytis species such as, for example, Botrytis cinerea;     diseases of the plant tubers, caused by, for example, -   Rhizoctonia species such as, for example, Rhizoctonia solani;     diseases caused by bacterial pathogens such as, for example, -   Xanthomonas species such as, for example, Xanthomonas campestris pv.     oryzae; -   Pseudomonas species such as, for example, Pseudomonas syringae pv.     lachrymans;     Erwinia species such as, for example, Erwinia amylovora.

The following diseases of soybeans can preferably be controlled:

Fungal diseases on leaves, stems, pods and seeds caused by, for example,

-   alternaria leaf spot (Alternaria spec. atrans tenuissima),     anthracnose (Colletotrichum gloeosporoides dematium var. truncatum),     brown spot (Septoria glycines), cercospora leaf spot and blight     (Cercospora kikuchii), choanephora leaf blight (Choanephora     infundibulifera trispora (syn.)), dactuliophora leaf spot     (Dactuliophora glycines), downy mildew (Peronospora manshurica),     drechslera blight (Drechslera glycini), frogeye leaf spot     (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina     trifolii), phyllostica leaf spot (Phyllosticta sojaecola), powdery     mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta     glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia     solani), rust (Phakopsora pachyrhizi), scab (Sphaceloma glycines),     stemphylium leaf blight (Stemphylium botryosum), target spot     (Corynespora cassiicola);     fungal diseases on roots and the stem base caused by, for example, -   black root rot (Calonectria crotalariae), charcoal rot (Macrophomina     phaseolina), fosarium blight or wilt, root rot, and pod and collar     rot (Fusariurn oxysporum, Fusarium orthoccras, Fusarium semitectum,     Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus     terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem     blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum     var. caulivora), phytophthora rot (Phytophthora megasperma), brown     stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum,     Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium     ultimum), rhizoctonia root rot, stem decay, and damping-off     (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia     sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii),     thielaviopsis root rot (Thielaviopsis basicola).

The active compounds according to the invention also have a potent strengthening effect in plants. They are therefore suitable for mobilizing the plants' defences against attack by undesired microorganisms.

Plant-strengthening (resistance-inducing) substances are understood as meaning, in the present context, those substances which are capable of stimulating the defence system of plants in such a way that, when subsequently inoculated with undesired microorganisms, the heated plants display a substantial degree of resistance to these microorganisms.

In the present case, undesired microorganisms are understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment. The period of time within which their protection is effected is generally extended from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.

The fact that the active compounds, at the concentrations required for the controlling of plant diseases, are well tolerated by plants permits the treatment of aerial plant parts, of vegetative propagation material and seed, and of the soil.

In this context, the active compounds according to the invention can be employed particularly successfully for controlling cereal diseases such as, for example, against Puccinia species and of diseases in viticulture, fruit production and vegetable production such as, for example against Botrytis, Venturia or Alternaria species.

The active compounds according to the invention are also suitable for increasing the yield. Moreover, they display a low degree of toxicity and are well tolerated by plants.

If appropriate, the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be employed as intermediates and precursors for the synthesis of further active compounds.

All plants and plant parts can be treated in accordance with the invention. Plants are understood as meaning, in the present context, all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or else by biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant varieties capable or not capable of being protected by Plant Breeders' rights. Plant parts are understood as meaning all aerial and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, steins, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

The treatment according to the invention with the active compounds, of the plants and plant parts, is carried out directly or by acting on their environment, habitat, or store by the customary treatment methods, for example by immersion, spraying, vaporizing, fogging, broadcasting, painting on and, in the case of propagation material, in particular in the case of seeds, furthermore by coating with one or more coats.

In the protection of materials, the substances according to the invention can be employed for protecting industrial materials against attack and destruction by undesired microorganisms.

In the present context, industrial materials are understood as meaning non live materials which have been made for use in technology. For example, industrial materials which are to be protected by active compounds according to the invention from microbial modification or destruction can be glues, sizes, paper and board, textiles, leather, timber, paints and plastic articles, cooling lubricants and other materials which are capable of being attacked or destroyed by microorganisms. Parts of production plants, for example cooling-water circuits, which can be adversely affected by the multiplication of microorganisms may also be mentioned within the materials to be protected. Industrial materials which may be mentioned with preference for the purposes of the present invention are glues, sizes, paper and board, leather, timber, paints, cooling lubricants and heat-transfer fluids, especially preferably wood.

Microorganisms which are capable of bringing about a degradation or modification of the industrial materials and which may be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compounds according to the invention are preferably active against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

Examples which may be mentioned are microorganisms of the following genera:

-   Alternaria such as Alternaria tenuis, -   Aspergillus such as Aspergillus niger, -   Chaetomium such as Chaetomium globosum, -   Coniophora such as Coniophora puetana, -   Lentinus such as Lentinus tigrinus, -   Penicillium such as Penicillium glaucum, -   Polyporus such as Polyporus versicolor, -   Aureobasidium such as Aureobasidium pullulans, -   Sclerophoma such as Sclerophoma pityophila, -   Trichoderma such as Trichoderma viride, -   Escherichia such as Escherichia coli, -   Pseudomonas such as Pseudomonas aeruginosa, -   Staphylococcus such as Staphylococcus aureus.

Depending on their respective physical and/or chemical properties, the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, and also ULV cold- and warm-fogging formulations.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, pressurized liquefied gases and/or solid carriers, optionally with the use of surface-active agents, that is emulsifers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ for example organic solvents as cosolvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water. Liquefied gaseous extenders or carriers are those liquids which are gaseous at ambient temperature and at atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons and also butane, propane, nitrogen and carbon dioxide. As solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, pumice, marble, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. As emulsifiers and/or foam formers there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates. As dispersants there are suitable: for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used as a mixture with known fungicides, bactericides, acaricides, nematicides, or insecticides, for example, to improve the activity spectrum or prevent the development of resistance. In many instances, synergistic effects are obtained, i.e. the activity of the mixture exceeds the activity of the individual components.

Examples of co-components in mixtures are the following compounds:

Fungicides:

-   1) Nucleic acid synthesis inhibitors: for example benalaxyl,     benalaxyl-M, bupirimate, elozylacon, dimethirimol, ethirimol,     furalaxyl, hymexazol, mefenoxam, metalaxyl, metalaxyl-M, ofurace,     oxadixyl, oxolinic acid; -   2) mitosis and cell division inhibitors: for example benomyl,     carbendazim, diethofencarb, ethaboxam, fuberidazole, pencycuron,     thiabendazole, thiophanate-methyl, zoxamide; -   3) respiration inhibitors (inhibitors of the respiratory chain): -   3.1) inhibitors which act on complex I of the respiratory chain: for     example diflumetorim; -   3.2) inhibitors which act on complex II of the respiratory chain:     for example boscalid/nicobifen, carboxin, fenfuram, flutolanil,     furametpyr, furmecyclox, mepronil, oxycarboxin, penthiopyrad,     thifluzamide; -   3.3) inhibitors which act on complex III of the respiratory chain:     for example amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin,     enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl,     metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,     trifloxystrobin; -   4) decouplers: for example dinocap, fluazinam, meptyldinocap; -   5) ATP production inhibitors: for example fentin acetate, fentin     chloride, fentin hydroxide, silthiofam; -   6) amino acid and protein biosynthesis inhibitors: for example     andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin     hydrochloride hydrate, mepanipyrim, pyrimethanil; -   7) signal transduction inhibitors: for example fenpiclonil,     fludioxonil, quinoxyfen; -   8) lipid and membrane synthesis inhibitors: for example biphenyl,     chlozolinate, edifenphos, iodocarb, iprobenfos, iprodione,     isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride,     pyrazophos, tolclofos-methyl, vinclozolin; -   9) inhibitors of ergosterol biosynthesis: for example aldimorph,     azaconazole, bitertanol, bromuconazole, cyproconazole,     diclobutrazole, difenoconazole, diniconazole, diniconazole-M,     dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol,     fenbuconazole, fenhexamid, fenpropidin, fenpropimorph,     fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole,     furconazole-cis, hexaconazole, imazalil, imazalil sulfate,     imibenconazole, ipconazole, metconazole, myclobutanil, naftifine,     nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole,     prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox,     simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole,     triadimefon, triadimenol, tridemorph, triflumizole, triforine,     triticonazole, uniconazole, viniconazole, voriconazole; -   10) cell wall synthesis inhibitors: for example benthiavalicarb,     dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim,     validamycin A; -   11) melanin biosynthesis inhibitors: for example carpropamid,     diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole; -   12) resistance inductors: for example acibenzolar-S-methyl,     probenazole, tiadinil; -   13) compounds with multi-site activity: for example Bordeaux     mixture, captafol, captan, chlorothalonil, copper naphthenate,     copper oxide, copper oxychloride, copper preparations such as, for     example, copper hydroxide, copper sulphate, dichlofluanid,     dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet,     guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate,     iminoctadine triacetate, mancopper, mancozeb, maneb, metiram,     metiram zinc, oxine-copper, propineb, sulphur and sulphur     preparations such as, for example, calcium polysulphide, thiram,     tolylfluanid, zineb, ziram; -   14) a compound selected from the following enumeration:     N-methyl-(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)acetamid,     N-methyl-(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)acetamide,     1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,     1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylate,     2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide,     2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,     2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,     2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)nicotinamide,     2-phenylphenol and salts thereof,     3,4,5-trichloropyridine-2,6-dicarbonitrile,     3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide,     3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,     5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo-[1,5-a]pyrimidine-7-amine,     5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluoropheny)[1,2,4]triazolo-[1,5-a]pyrimidine,     5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-pyrimidine-7-amine,     8-hydroxyquinoline sulphate, benthiazole, bethoxazin, capsimycin,     carvone, quinomethionate, cufraneb, cyflufenamid, cymoxanil,     dazomet, debacarb, dichlorophen, diclomezine, dicloran, difenzoquat,     difenzoquat methylsulphate, diphenylamine, ferimzone, flumetover,     fluopicolide, fluoroimide, flusulfamide, fosetyl-aluminium,     fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin,     methasulfocarb, methyl     (2-chloro-5-{(1E)-N-[(6-methylpyridin-2-yl)methoxy]ethanimido-yl}benzyl)carbamate,     methyl     (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]-phenyl}-3-methoxyacrylate,     methyl     1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,     methyl     3-(4-chlorophenyl)-3-{[N-(isopropoxycarbonyl)valyl]amino}propanoate,     methyl isothiocyanate, metrafenone, mildiomycin,     N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,     N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxy-benzamide,     N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulphonamide,     N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,     N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,     N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,     N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N²-(methylsulphonyl)valinamide,     N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluoropheny]methyl}-2-phenylacetamide,     N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,     natamycin, nickel dimethyl dithiocarbamate, nitrothal-isopropyl,     O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}     1H-imidazole-1-carbothioate, octhilinone, oxamocarb, oxyfenthiin,     pentachlorophenol and salts, phosphoric acid and its salts,     piperalin, propamocarb fosetylate, propanosine-sodium, proquinazid,     pyrrolnitrine, quintozene, tecloftalam, tecnazene, triazoxide,     trichlamide, zarilamid,     Bactericides:

Bronopol, dichlorophen, nitrapyrin, nickel dimethyl dithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.

Insecticides/Acaricides/Nematicides:

-   1. Acetylcholine esterase (AChE) inhibitors     -   1.1 Carbamates (for example alanycarb, aldicarb, aldoxycarb,         allyxycarb, aminocarb, azamethiphos, bendiocarb, benfuracarb,         bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl,         carbofuran, carbosulfan, chloethocarb, coumaphos, cyanofenphos,         cyanophos, dimetilan, ethiofencarb, fenobucarb, fenothiocarb,         formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb,         methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur,         thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb)     -   1.2 Organophosphates (for example acephate, azamethiphos,         azinphos (-methyl, -ethyl), bromophosethyl, bromfenvinfos         (-methyl), butathiofos, cadusafos, carbophenothion,         chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos         (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos,         chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon,         dialifos, diazinon, dichlofenthion, dichlorvos/DDVP,         dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos,         disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur,         fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,         fonofos, formothion, fosmethilan, fosthiazate, heptenophos,         iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl         O-salicylate, isoxathion, malathion, mecarbam, methacrifos,         methamidophos, methidathion, mevinphos, monocrotophos, naled,         omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl),         phenthoate, phorate, phosalone, phosmet, phosphamidon,         phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos,         propaphos, propetamphos, prothiofos, prothoate, pyraclofos,         pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep,         sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos,         thiometon, triazophos, triclorfon, vamidothion) -   2. Sodium channel modulators/voltage-dependent sodium channel     blockers     -   2.1 Pyrethroids (for example acrinathrin, allethrin         (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin,         bioallethrin, bioallethrin-S-cyclopentyl isomer,         bioethanomethrin, biopermethrin, biopermethrin, chlovaporthrin,         cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin,         cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-,         beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin,         empenthrin (1R isomer), esfenvalerate, etofenprox, fenfluthrin,         fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate,         flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox,         gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin,         metofluthrin, permethrin (cis-, trans-), phenothrin (1R         transisomer), prallethrin, profluthrin, protrifenbute,         pyresmethrin, resmethrin, RU 15525, silafluofen, taufluvalinate,         tefluthrin, terallethrin, tetramethrin (1R isomer),         tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum))     -   2.2 Oxadiazines (for example indoxacarb) -   3. Acetylcholine receptor agonists/antagonists     -   3.1 Chloronicotinyls/neonicotinoids (for example acetamiprid,         clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine,         thiacloprid, thiamethoxam)     -   3.2 Nicotine, bensultap, cartap -   4. Acetylquoline receptor modulators     -   4.1 Spinosyns (for example spinosad) -   5. GABA-controlled chloride channel antagonists     -   5.1 Cyclodiene organochlorines (for example camphechlor,         chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane,         methoxychlor     -   5.2 Fiprols (for example acetoprole, ethiprole, fipronil,         vaniliprole) -   6. Chloride channel activators     -   6.1 Mectins (for example abamectin, avermectin, emamectin,         emamectin benzoate, ivermectin, milbemectin, milbemycin) -   7. Juvenile hormone mimetics -    (for example diofenolan, epofenonane, fenoxycarb, hydroprene,     kinoprene, methoprene, pyriproxifen, triprene) -   8. Ecdysone agonists/disruptors     -   8.1 Diacylhydrazines (for example chromafenozide, halofenozide,         methoxyfenozide, tebufenozide) -   9. Chitin biosynthesis inhibitors     -   9.1 Benzoylureas (for example bistrifluron, chlofluazuron,         diflubenzuron, fluazuron, flucycloxuron, flufenoxuron,         hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron,         teflubenzuron, triflumuron)     -   9.2 Buprofezin     -   9.3 Cyromazine -   10. Inhibitors of oxidative phosphorylation, ATP disrupters     -   10.1 Diafenthiuron     -   10.2 Organotins (for example azocyclotin, cyhexatin, fenbutatin         oxide) -   11. Uncouplers of oxidative phosphorylation by interrupting the     H-proton gradient     -   11.1 Pyrroles (for example chlorfenapyr)     -   11.2 Dinitrophenols (for example binapacyrl, dinobuton, dinocap,         DNOC) -   12. Site-I electron transport inhibitors     -   12.1 METIs (for example fenazaquin, fenpyroximate, pyrimidifen,         pyridaben, tebufenpyrad, tolfenpyrad)     -   12.2 Hydramethylnon     -   12.3 Dicofol -   13. Site-II electron transport inhibitors     -   13.1 Rotenone -   14. Site-III electron transport inhibitors     -   14.1 Acequinocyl, fluacrypyrim -   15. Microbial disrupters of the insect gut membrane -    Bacillus thuringiensis strains -   16. Fat synthesis inhibitors     -   16.1 Tetronic acids (for example spirodiclofen, spiromesifen)     -   16.2 Tetramic acids (for example         3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl         ethyl carbonate (also known as: carbonic acid,         3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro-[4.5]dec-3-en-4-yl         ethyl ester, CAS Reg. No.: 382608-10-8) and carbonic acid,         cis-3-(2,5-dimethyl-phenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl         ethyl ester (CAS Reg.-No.: 203313-25-1)] -   17. Carboxamides -    (for example flonicamid) -   18. Octopaminergic agonists -    (for example amitraz) -   19. Inhibitors of magnesium-stimulated ATPase (for example     propargite) -   20. Phthalamides -    (for example     N²-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-N¹-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide     (CAS Reg.-No.: 272451-65-7), flubendiamide) -   21. Nereistoxin analogues -    (for example thiocyclam hydrogen oxalate, thiosultap sodium) -   22. Biologicals, hormones or pheromones -    (for example azadirachtin, Bacillus spec., Beauveria spec.,     codlemone, Metarhizium spec., Paecilomyces spec., thuringiensin,     Verticillium spec.) -   23. Active compounds with unknown or unspecific mechanisms of action     -   23.1 Fumigants (for example aluminium phosphide, methyl bromide,         sulfuryl fluoride)     -   23.2 Selective antifeedants (for example cryolite, flonicamid,         pymetrozine)     -   23.3 Mite growth inhibitors (for example clofentezine,         etoxazole, hexythiazox)     -   23.4 Amidoflumet, benclothiaz, benzoximate, bifenazate,         bromopropylate, buprofezin, quinomethionate, chlordimeform,         chlorobenzilate, chloropicrin, clothiazoben, cycloprene,         cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine,         flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure,         metoxadiazone, petroleum, piperonyl butoxide, potassium oleate,         pyrafluprole, pyridalyl, pyriprole, sulfluramid, tetradifon,         tetrasul, triarathene, verbutin, furthermore the compound         3-methyl-phenyl propylcarbamate (tsumacide Z), the compound         3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile         (CAS Reg. No. 185982-80-3) and the corresponding 3-endo isomer         (CAS Reg. No. 185984-60-5) (cf. WO 96/37494, WO 98/25923), and         preparations which contain insecticidally active plant extracts,         nematodes, fungi or viruses.

A mixture with other known active compounds such as herbicides, or with fertilizers and growth regulators, safeners or semiochemicals is also possible.

In addition, the compounds of the formula (I) according to the invention also have very good antimycotic activity. They have a very broad antimycotic spectrum of action, in particular against dermatophytes and budding fungi, moulds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The enumeration of these fungi is no restriction whatsoever of the mycotic spectrum which can be controlled and is provided by illustration only.

The active compounds can be employed as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are applied in the customary manner, for example by pouring, spraying, atomizing, broadcasting, dusting, foaming, painting on and the like. It is furthermore possible to apply the active compounds by the ultra-low-volume method, or to inject the active compound preparation or the active compound itself into the soil. The seed of the plant can also be treated.

When employing the active compounds according to the invention as fungicides, the application rates can be varied within a substantial range, depending on the type of application. In the treatment of plant parts, the application rates of active compound are generally between 0.1 and 10 000 g/ha, preferably between 10 and 1000 g/ha. For the treatment of seed, the application rates of active compound are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. For treating the soil, the application rates of active compound are generally between 0.1 and 10 000 g/ha, preferably between 1 and 5000 g/ha.

As already mentioned above, all plants and their parts can be treated in accordance with the invention. In a preferred embodiment, plant species and plant varieties which are found in the wild or are obtained by traditional biological breeding methods, such as hybridization or protoplast fusion, and parts of the former are treated. In a further preferred embodiment, transgenic plants and plant varieties which have been obtained by recombinant methods, if appropriate in combination with traditional methods (genetically modified organisms) and their parts are treated. The term “parts” or “parts of plants” or “plant parts” has been illustrated above.

Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are understood as meaning plants with new properties (“traits”) which have been obtained by conventional cultivation, by mutagenesis or else by recombinant DNA techniques. These may be cultivars, breeds, biotypes or genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also result in superadditive (“synergistic”) effects. Thus, for example, reduced application rates and/or extensions of the activity spectrum and/or an increase in the activity of the substances and compositions that can be used according to the invention, better plant growth, more developed root system, higher resistance of the plant variety or plant cultivar, increased growth of shoots, higher plant vitality, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, larger fruit, increased plant size, greener leaf colour, earlier blossoming, better quality and/or a higher nutritional value of the harvested products, higher sugar concentration in the fruits, better storage stability and/or processability of the harvested products which exceed the effects which were actually to be expected are possible.

The preferred transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are to be treated according to the invention include all plants which, as a result of the recombinant modification, received genetic material which imparted particularly advantageous useful properties (“traits”) to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, easier harvesting, accelerated maturation, higher yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized in particular are increased defence of the plants against insects, arachnids, nematodes, slugs and snails as the result of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as “Bt plants”). Traits which are also particularly emphasized are the increased defence of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and the correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the “PAT” gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of “Bt plants” which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosates, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinothricin, for example oilseed rape), IMI® (tolerance to imidazolinoses) and STS® (tolerance to sulfonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned also include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which cultivars will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) or the active compound mixtures according to the invention. The preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

The preparation and the use of the active compounds according to the invention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1 Preparation of 2-(1,3-dimethylbutyl)cyclohexanamine

5 g of Ru/C (5%) are added to a solution comprising 20.0 g (0.113 mol) of 2-(1,3-dimethylbutyl)aniline in 300 ml of tetrahydrofuran, and the mixture is hydrogenated with 100 bar of hydrogen at 120° C. for 24 hours. After cooling to room temperature, the catalyst is filtered off through Celite 545 and the product is concentrated under reduced pressure. This gives 19.1 g (92.4% of theory) of 2-(1,3-dimethylbutyl)cyclohexanamine having a purity of 100% according to HPLC and a log P (pH 2.3) of 4.07.

Preparation of 4-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)cyclohexyl]-2-methyl-1,3-thiazole-5-carboxamide

At room temperature, 0.104 g (0.82 mmol) of oxalyl chloride is added dropwise to a solution of 0.16 g (0.82 mmol) of 4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxylic acid and a drop of DMF in 15 ml of dichloromethane, and the mixture is stirred at room temperature for 1 hour.

At room temperature, the acid chloride solution described above is added dropwise to a solution comprising 0.15 g (0.82 mmol) of 2-(1,3-dimethylbutyl)cyclohexanamine and 0.25 g (0.0025 mol) of triethylamine in 5 ml of dichloromethane, and the reaction mixture is stirred at room temperature for 12 hours.

The mixture is washed twice with in each case 10 ml of water, dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel using n-hexane/methyl tert-butyl ether (3:1). This gives 0.12 g (38.9% of theory) of 4-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)cyclohexyl]-2-methyl-1,3-thiazole-5-carboxamide as a mixture of diastereomers having a content of 95% according to HPLC and a log P (pH 2.3) of 4.45/4.53.

TABLE 1 (I-c)

logP*/ m.p. No. s R¹ R² R³ R⁴ R⁵ A (° C.) I-c- 1 1 H CH₃ CH₃ CH₃ H

4.15 62- 65° C. I-c- 2 1 H CH₃ CH₃ CH₃ H

4.04 94- 98° C. I-c- 3 1 H CH₃ CH₃ CH₃ H

4.66/ 4.71 I-c- 4 1 H CH₃ CH₃ CH₃ H

4.45/ 4.53 I-c- 5 1 H CH₃ CH₃ CH₃ H

4.12/ 4.23 I-c- 6 1 H CH₃ CH₃ CH₃ H

4.10/ 4.53 I-c- 7 1 H CH₃ CH₃ CH₃ H

3.88/ 4.28 I-c- 8 1 H CH₃ CH₃ CH₃ H

4.72/ 4.88 I-c- 9 1 H CH₃ CH₃ CH₃ H

4.73/ 5.15 I-c- 10 1 H CH₃ CH₃ CH₃ H

4.52/ 4.83 I-c- 11 1 H CH₃ CH₃ CH₃ H

4.45/ 4.83 I-c- 12 1 H CH₃ CH₃ CH₃ H

4.27/ 4.58 I-c- 13 1 H CH₃ CH₃ CH₃ H

4.49/ 4.67 I-c- 14 1 H CH₃ CH₃ CH₃ H

3.18/ 3.47 I-c- 15 1 H CH₃ CH₃ CH₃ H

4.75/ 4.92 I-c- 16 1 H CH₃ CH₃ CH₃ H

4.60/ 4.83 I-c- 17 1 H CH₃ CH₃ CH₃ H

4.49/ 4.75 I-c- 18 1 H CH₃ CH₃ CH₃ H

4.46/ 4.86 I-c- 19 1 H H CH₃ CH₃ CH₃

4.22 I-c- 20 1 H CH₃ CH₃ CH₃ H

4.58/ 5.00 I-c- 21 1 H CH₃ CH₃ CH₃ H

4.10/ 4.43 I-c- 22 1 H CH₃ CH₃ CH₃ H

 3.9/ 4.32 I-c- 23 1 H H CH₃ CH₃ CH₃

4.71 I-c- 24 1 H H CH₃ CH₃ CH₃

4.72 I-c- 25 1 H H CH₃ CH₃ CH₃

4.55 I-c- 26 1 H CH₃ CH₃ CH₃ H

4.06 I-c- 27 1 H CH₃ CH₃ CH₃ CH₃

4.44/ 4.64 I-c- 28 1 H CH₃ CH₃ CH₃ CH₃

4.17/ 4.33/ 4.47/ 4.55 I-c- 29 1 H CH₃ CH₃ CH₃ CH₃

4.94/ 4.98/ 5.08 I-c- 30 1 H CH₃ CH₃ CH₃ CH₃

5.07/ 5.22 I-c- 31 1 H CH₃ CH₃ CH₃ CH₃

4.29/ 4.37/ 4.68 I-c- 32 1 H CH₃ CH₃ CH₃ CH₃

4.97/ 5.07/ 5.36 I-c- 33 1 H CH₃ CH₃ CH₃ CH₃

4.54/ 4.63/ 4.87 I-c- 34 1 H CH₃ CH₃ CH₃ CH₃

3.42/ 3.54/ 3.66/ 3.74 I-c- 35 1 H CH₃ CH₃ CH₃ CH₃

4.37/ 4.48/ 4.74/ 4.82 I-c- 36 1 H CH₃ CH₃ CH₃ CH₃

4.15/ 4.27/ 4.48/ 4.57 I-c- 37 1 H CH₃ CH₃ CH₃ CH₃

4.70/ 4.80/ 5.11/ 5.16 I-c- 38 1 H CH₃ CH₃ CH₃ CH₃

4.15/ 4.21/ 4.35 I-c- 39 1 H H CH₃ CH₃ CH₃

4.66 I-c- 40 1 H H CH₃ CH₃ CH₃

4.45 I-c- 41 1 H H CH₃ CH₃ CH₃

4.88 I-c- 42 1 H H CH₃ CH₃ CH₃

4.27 I-c- 43 1 H H CH₃ CH₃ CH₃

3.29/ 3.42 I-c- 44 1 H CH₃ CH₃ CH₃ CH₃

4.73/ 4.83/ 5.08 I-c- 45 1 H CH₃ CH₃ CH₃ CH₃

4.04/ 4.19/ 4.36 I-c- 46 1 H CH₃ CH₃ CH₃ CH₃

4.78/ 4.86/ 4.95 I-c- 47 1 H CH₃ CH₃ CH₃ CH₃

4.83/ 4.90/ 5.09/ 5.25 I-c- 48 1 H CH₃ CH₃ CH₃ H

4.80/ 4.85/ 4.98/ 5.11 I-c- 49 1 H CH₃ CH₃ CH₃ CH₃

4.77/ 4.85/ 5.00 I-c- 50 1 H CH₃ CH₃ CH₃ CH₃

5.03/ 5.11/ 5.40 I-c- 51 1 H CH₃ CH₃ CH₃ CH₃

4.87/ 4.94/ 5.09 I-c- 52 1 H CH₃ CH₃ CH₃ CH₃

4.91/ 5.11/ 5.16 I-c- 53 1 H CH₃ CH₃ CH₃ CH₃

4.95/ 5.12/ 5.17 I-c- 54 1 H CH₃ CH₃ CH₃ CH₃

4.94/ 5.00/ 5.18 I-c- 55 1 H CH₃ CH₃ CH₃ CH₃

4.36/ 4.52/ 4.70 I-c- 56 1 H H CH₃ CH₃ H

4.6  I-c- 57 1 H H CH₃ CH₃ H

4.19 I-c- 58 1 H H CH₃ CH₃ H

3.76 I-c- 59 1 H H CH₃ CH₃ H

4.46 I-c- 60 1 H H CH₃ CH₃ H

3.79 I-c- 61 1 H H CH₃ CH₃ H

4.59 I-c- 62 1 H H CH₃ CH₃ H

3.95 I-c- 63 1 H H CH₃ CH₃ H

3.19 I-c- 64 1 H H CH₃ CH₃ H

4.42 I-c- 65 1 H H CH₃ CH₃ H

4.28 I-c- 66 1 H H CH₃ CH₃ H

4.56 I-c- 67 1 H H CH₃ CH₃ H

4.82 I-c- 68 1 H H CH₃ CH₃ H

4.51 I-c- 69 1 H H CH₃ CH₃ H

4.61 I-c- 70 1 H H CH₃ CH₃ H

4.66 I-c- 71 1 H H CH₃ CH₃ H

4.54 I-c- 72 1 H H CH₃ CH₃ H

4.8  I-c- 73 1 H H CH₃ CH₃ H

4.52 I-c- 74 1 H H CH₃ CH₃ H

4.47 I-c- 75 2 H H CH₃ CH₃ H

4.22 I-c- 76 2 H H CH₃ CH₃ H

4.66 I-c- 77 1 H H CH₃ CH₃ H

4.07 I-c- 78 2 H H CH₃ CH₃ H

4.95 I-c- 79 2 H H CH₃ CH₃ H

5.06 I-c- 80 1 H H CH₃ CH₃ H

5.16/ 5.47 I-c- 81 1 H H CH₃ CH₃ CH₃

4.24 I-c- 82 1 H H CH₃ CH₃ CH₃

4.72 I-c- 83 2 H H CH₃ CH₃ H

4.40 I-c- 84 2 H H CH₃ CH₃ H

4.30 I-c- 85 2 H H CH₃ CH₃ H

5.34 I-c- 86 2 H H CH₃ CH₃ H

5.05 I-c- 87 2 H H CH₃ CH₃ H

4.86 I-c- 88 1 H H CH₃ CH₃ CH₃

5.35 I-c- 89 1 H H CH₃ CH₃ CH₃

4.89 I-c- 90 1 H H CH₃ CH₃ CH₃

I-c- 91 1 H H CH₃ CH₃ CH₃

I-c- 92 1 H H CH₃ CH₃ CH₃

4.79 I-c- 93 1 H H CH₃ CH₃ CH₃

4.12/ 4.47 I-c- 94 1 H H CH₃ CH₃ CH₃

4.06/ 4.28 I-c- 95 1 H H CH₃ CH₃ CH₃

5.03 I-c- 96 1 H CH₃ CH₃ CH₃ H

5.03 I-c- 97 1 H H CH₃ CH₃ CH₃

4.87 I-c- 98 1 H CH₃ CH₃ CH₃ H

4.92 I-c- 99 1 H CH₃ CH₃ CH₃ CH₃

5.29 I-c- 100 1 H H CH₃ CH₃ CH₃

4.77 For all compounds of this Table 1, n = 0. *logP values are given for the main diastereomer or, if detectable, for the individual diastereomers:

TABLE 2 (I-d)

logP*/ No. s R¹ R² R³ R⁴ R⁵ A m.p. (° C.) I-d-1 1 H H CH₃ CH₃ H

4.22/4.53 For all compounds of this Table 2, n = 0. *logP values are given for the main diastereomer or, if detectable, for the individual diastereomers:

TABLE 3 (I-k)

logP*/ m.p. No. s R¹ R² R⁴⁹ R⁵⁰ R⁵¹ A (° C.) I-k-1 1 H H CH₃ CH₃ CH₃

4.15 I-k-2 1 H CH₃ CH₃ CH₃ CH₃

4.51 I-k-3 1 H H CH₃ CH₃ CH₃

5.13 I-k-4 1 H CH₃ CH₃ CH₃ CH₃

5.44 I-k-5 1 H H CH₃ CH₃ CH₃

4.25/ 4.54 I-k-6 1 H CH₃ CH₃ CH₃ CH₃

4.56 I-k-7 1 H H CH₃ CH₃ CH₃

4.82/ 5.06 I-k-8 1 H CH₃ CH₃ CH₃ CH₃

5.13 For all compounds of this Table 3, n = 0. *the logP values are given for the main diastereomer or, if detectable, for the individual diastereomers:

The stated log P values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (High Performance Liquid Chromatography) on a reverse-phase column (C 18). Temperature: 43° C.

Mobile phases for the determination in the acidic range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known log P values (determination of the log P values by the retention times using linear interpolation between two successive alkanones).

The lambda max values were determined in the maximum of the chromatographic signals using the UV spectra from 200 nm to 400 nm.

USE EXAMPLES Example A Podosphaera Test (Apple)/Protective

Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Podosphaera leucotricha. The plants are then placed in a greenhouse at about 23° C. and a relative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

TABLE A Podosphaera test (apple)/protective Application rate of active Effi- Active compound compound cacy according to the invention in g/ha in % (I-c-4)

100 100 (I-c-5)

100 100 (I-c-7)

100 100 (I-c-1)

100  88

Example B Venturia Test (Apple)/Protective

Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants ate inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain in an incubation cabinet as about 20° C. and 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse at about 21° C. and a relative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

TABLE B Venturia test (apple)/protective Application rate of active Effi- Active compound compound cacy according to the invention in g/ha in % (I-c-4) 

100  98 (I-c-5) 

100 100 (I-c-6) 

100  99 (I-c-7) 

100 100 (I-c-11)

100  90 (I-c-1) 

100 100

Example C Botrytis Test (Bean)/Protective

Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on 2 small pieces of agar colonized by Botrytis cinerea are placed onto each leaf. The inoculated plants are placed in a dark chamber at about 20° C. and 100% relative atmospheric humidity.

2 days after the inoculation, the size of the infected areas on the leaves is evaluated. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

TABLE C Botrytis test (bean)/protective Application rate of active compound Effi- Active compound in cacy according to the invention g/ha in % (I-c-4) 

500 95 (I-c-5) 

500 99 (I-c-6) 

500 90 (I-c-7) 

500 94 (I-c-11)

500 96

Example D Puccinia Test (Wheat)/Protective

Solvent: 50 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain in an incubation cabinet at 20° C. and 100% relative atmospheric humidity for 48 hours. The plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of 80%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

TABLE D Puccinia test (wheat)/protective Application rate of active Effi- Active compound compound cacy according to the invention in g/ha in % (I-c-3) 

500 100 (I-c-4) 

500 100 (I-c-14)

500 100 (I-c-5) 

500 100 (I-c-6) 

500 100 (I-c-7) 

500 100 (I-c-9) 

500 100 (I-c-10)

500 100 (I-c-12)

500 100 (I-c-1) 

500 100

Example E Alternaria Test (Tomato)/Protective

Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young tomato plants are sprayed with the preparation of active compound at the stated application rate. 1 day after the treatment, the plants are inoculated with a spore suspension of Alternaria solani and then remain at 100% relative atmospheric humidity and 20° C. for 24 h. The plants then remain at 96% relative atmospheric humidity and a temperature of 20° C.

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

TABLE E Alternaria test (tomato)/protective Application rate of active Effi- Active compound compound cacy according to the invention in g/ha in % (I-c-4) 

750 100 (I-c-14)

750 100 (I-c-5) 

750 100 (I-c-7) 

750 100 (I-c-10)

750 100 

The invention claimed is:
 1. A compound of the formula (I)

in which X represents —CR³R⁴R⁵, s represents 1 or 2, R¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms; represents formyl, formyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl; represents halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl, having in each case 1 to 13 fluorine, chlorine or bromine atoms; represents (C₁-C₈-alkyl)carbonyl, (C₁-C₈-alkoxy)carbonyl, (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, or (C₃-C₈-cycloalkylcarbonyl; represents (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl, (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, or (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine or bromine atoms; or represents —C(═O)C(═O)R⁶, —CONR⁷R⁸ or —CH₂NR⁹R¹⁰, L represents

in which n represents 0, 1, 2, 3, or 4, Y¹ represents fluorine, chlorine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or difluoromethyl, wherein Y¹ is identical or different if n is greater than 1, R² represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 9 fluorine, chlorine or bromine atoms, R³ represents halogen, C₁-C₈-alkyl or C₁-C₆-haloalkyl, having 1 to 13 fluorine, chlorine or bromine atoms, R⁴ represents halogen, C₁-C₈-alkyl or C₁-C₆-haloalkyl, having 1 to 13 fluorine, chlorine or bromine atoms, R⁵ represents hydrogen, halogen, C₁-C₈-alkyl or C₁-C₆-haloalkyl, having 1 to 13 fluorine, chlorine or bromine atoms, or R³ and R⁴ together with the carbon atom to which they are attached form a 3- to 6-membered carbocyclic, heterocyclic, saturated or unsaturated ring, each of which is optionally substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy, R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, R⁷ and R⁸ independently of one another each represent hydrogen, C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, or R⁷ and R⁸ together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C₁-C₄-alkyl, where the heterocycle optionally further contains 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR¹¹, R⁹ and R¹⁰ independently of one another represent hydrogen, C₁-C₈-alkyl, or C₃-C₈-cycloalkyl; represents C₁-C₈-haloalkyl or C₃-C₈-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, or R⁹ and R¹⁰ together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C₁-C₄-alkyl, where the heterocycle optionally further contains 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR¹¹, R¹¹ represents hydrogen or C₁-C₆-alkyl, A represents a radical of the formula (A2)

in which R¹⁵ and R¹⁶ independently of one another represent hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R¹⁷ represents halogen, cyano or C₁-C₄-alkyl; or represents C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms, or A represents a radical of the formula (A3)

in which R¹⁸ and R¹⁹ independently of one another represent hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R²⁰ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl, having 1 to 5 halogen atoms, or A represents a radical of the formula (A4)

in which R²¹ represents hydrogen, halogen, hydroxyl, cyano, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio, having in each case 1 to 5 halogen atoms, or A represents a radical of the formula (A6)

in which R²⁴ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R²⁵ represents C₁-C₄ alkyl, Q¹ represents S (sulphur), O (oxygen), SO, SO₂ or CH₂, p represents 0, 1 or 2, provided that when p is 2, R²⁵ represents identical different radicals, or A represents a radical of the formula (A7)

in which R²⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A8)

in which R²⁷ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A9)

in which R²⁸ and R²⁹ independently of one another represent hydrogen, halogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl, having 1 to 5 halogen atoms, R³⁰ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A 10)

in which R³¹ and R³² independently of one another represent hydrogen, halogen, amino, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R³³ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A11)

in which R³⁴ represents hydrogen, halogen, amino, C₁-C₄-alkylamino, di-(C₁-C₄ alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R³⁵ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A12)

in which R³⁶ represents hydrogen, halogen, amino, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R³⁷ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A13)

in which R³⁸ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to halogen atoms, or A represents a radical of the formula (A14)

in which R³⁹ represents hydrogen or C₁-C₄-alkyl, R⁴⁰ represents halogen or C₁-C₄-alkyl, or A represents a radical of the formula (A18)

in which R⁴⁴ represents hydrogen, cyano, C₁-C₄-haloalkyl having 1 to 5 halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkylsulphonyl, di(C₁-C₄-alkyl)aminosulphonyl, C₁-C₆-alkylcarbonyl, or in each case optionally substituted phenylsulphonyl or benzoyl, R⁴⁵ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R⁴⁶ represents hydrogen, halogen, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, R⁴⁷ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms, or A represents a radical of the formula (A19)

in which R⁴⁸ represents C₁-C₄-alkyl.
 2. A process for preparing the compound according to claim 1, comprising reacting (a) a carboxylic acid derivative of the formula (II)

in which A is as defined in claim 1 and X¹ represents halogen or hydroxyl, with an aniline derivative of the formula (III)

in which R¹, L, R², R³, R⁴ and R⁵ are as defined in claim 1, optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binder and optionally in the presence of a diluent, or (b) a compound of the formula (I-a)

in which L, R², R³, R⁴, R⁵ and A are as defined in claim 1, with a halide of the formula (IV) R^(1A)—X²  (IV) in which R^(1A) represents C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; represents C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms; represents formyl, formyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)-carbonyl-C₁-C₃-alkyl, (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl, halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl or halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl, having in each case 1 to 13 fluorine, chlorine or bromine atoms; represents (C₁-C₈-alkyl)carbonyl, (C₁-C₈-alkoxy)carbonyl, (C₁-C₄-alkoxy-C₁-C₄-alkyl)-carbonyl, (C₃-C₈-cycloalkyl)carbonyl, (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl, (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, or (C₃-C₈-halocycloalkyl)carbonyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms; or represents —C(═O)C(═O)R⁶, —CONR⁷R⁸ or —CH₂NR⁹R¹⁰, R⁶, R⁷, R⁸, R⁹ and R¹⁰ are as defined in claim 1, X² represents chlorine, bromine or iodine, in the presence of a base and a diluent.
 3. A composition for controlling unwanted microorganisms, comprising at least one compound according to claim 1, and an extender, a surfactant, or a combination thereof.
 4. A method for controlling unwanted microorganisms, comprising applying 2-alkylcycloalk(en)ylcarboxamides of the formula (I) according to claim 1 to plants and plant parts directly or to their environment, habitat, or store.
 5. A method for controlling unwanted microorganisms, comprising contacting a compound according to claim 1 with the microorganisms or their habitat.
 6. A process for preparing compositions for controlling unwanted microorganisms, comprising mixing a compound according to claim 1 with an extender, a surfactant or a combination thereof.
 7. The compound of the formula (I) according to claim 1, wherein R¹ represents hydrogen, methyl, methoxymethyl, formyl, —CH₂—CHO, —(CH₂)₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂, —C(═O)CHO, —C(═O)C(═O)CH₃, —C(═O)C(═O)CH₂OCH₃, —C(═O)CO₂CH₃, or C(═O)CO₂CH₂CH₃, R² represents hydrogen, fluorine, chlorine, methyl, ethyl, or trifluoromethyl, R³ represents chlorine, methyl, ethyl, isopropyl, or trifluoromethyl, R⁴ represents chlorine, methyl, ethyl, isopropyl, or trifluoromethyl, and R⁵ represents hydrogen, chlorine, methyl, ethyl, isopropyl, or trifluoromethyl.
 8. The compound according to claim 1 is Compound I-c-4:


9. The method for controlling unwanted microorganisms according to claim 5, wherein the compound is Compound I-c-4:


10. The process for preparing the composition according to claim 6, wherein the compound is Compound I-c-4: 